New York Yankees center fielder Jacoby Ellsbury triples to right to drive in three runs.

New York Yankees center fielder Jacoby Ellsbury triples to right to drive in three runs. (Photo by Frank Jansky/Icon Sportswire)

As Major League Baseball general managers prepare to shell out massive contracts during the offseason, we decided to review some of the worst deals made over the last decade.

5. James Shields (four-year, $75 million deal with the Padres in 2015)

White Sox fans not only suffered through the last 2 1/2 years of James Shields’ contract after he lost his form (16-35, 5.31 ERA in 77 games in Chicago), but they watched their club deal Fernando Tatis Jr. away to the Padres for the right to have Big Game James. Ouch.

4. Ian Desmond (five-year, $70 million deal with the Rockies in 2017)

The Rockies’ signing of Ian Desmond seemed illogical from the outset, and he hasn’t delivered on the contract he signed in 2017. He played just 95 games in the first year of his deal and recorded a mediocre .701 OPS. Subsequent years have seen that figure rise to .729 and .788, but a supposedly juiced baseball may have helped, in addition to playing half his games at Coors Field.

3. Wei-Yin Chen (five-year, $80 million deal with the Marlins in 2016)

With just 102 appearances (53 starts) in four years as a Marlin, Wei-Yin Chen’s tenure in Miami has been an unmitigated disaster. The oft-injured southpaw is 13-19 with a 5.10 in four years for the Fish. The deal made sense at the time based on his numbers in Baltimore (46-32, 3.72 ERA over four seasons), but it’s surprising the Marlins haven’t cut bait with Chen, who is owed $22 million in 2020.

2. Pablo Sandoval (five-year, $95 million deal with the Red Sox in 2015)

A fan favorite in the Bay Area, Pablo Sandoval seemed out of his element in Boston from the start. He hit just .245 with 10 home runs in the first year of his contract and spent most of 2016 on the disabled list. Sandoval was cut midway through the 2017 season and reunited with the Giants. He had an .820 OPS in 2019, something the Red Sox would have killed for during his time at Fenway Park.

1. Jacoby Ellsbury (seven-year, $153 million deal with the Yankees in 2014)

It seemed like Jacoby Ellsbury could do it all during his time in Boston, as he hit for power (32 home runs in 2011), average (.297 over seven years) and even stole bases (52 in 2013). Despite some health concerns, the Yankees decided to swipe Ellsbury away from their division rival ahead of the 2014 campaign. The Oregon native brought his speed (102 stolen bases) to the Bronx but not much else, as his batting average dipped to .264 from 2014 to 2017. He’s missed each of the last two seasons for New York because of a torn labrum in his hip, among other ailments.


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